NP-MRD: Showing NP-Card for Calomelanone (NP0055302)

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Record Information

Version

2.0

Created at

2022-04-28 01:24:08 UTC

Updated at

2022-04-28 01:24:08 UTC

NP-MRD ID

NP0055302

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Calomelanone

Description

1-(2,6-Dihydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)propan-1-one belongs to the class of organic compounds known as 2'-hydroxy-dihydrochalcones. These are organic compounds containing dihydrochalcone skeleton that carries a hydroxyl group at the 2'-position. Thus, 1-(2,6-dihydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)propan-1-one is considered to be a flavonoid lipid molecule. Calomelanone is found in Greyia flanaganii, Notholaena sulphurea, Pityrogramma calomelanos , Pityrogramma chrysophylla , Pityrogramma ebenea, Pityrogramma tartarea, Populus trichocarpa, Populus x jackii and Sarcandra glabra. 1-(2,6-Dihydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)propan-1-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
    7.2703    0.5654    0.9831 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2325    1.3071    0.3579 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0152    0.6841    0.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7363   -0.6150    0.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4732   -1.1353    0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4817   -0.4029   -0.4051 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1254   -0.9940   -0.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3100   -0.7351    0.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0576   -1.2371    0.5089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1702   -2.4930    0.7999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2718   -0.5491    0.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3158    0.7726   -0.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1550    1.5118   -0.2081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5421    1.3966   -0.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7194    0.6987   -0.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8837    1.3809   -0.6863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1730    0.8527   -0.6934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6885   -0.6275   -0.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4894   -1.2323    0.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4885   -2.5942    0.5663 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7784    0.9022   -0.7409 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0121    1.4376   -0.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9232    0.3579    2.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1677    1.2310    1.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5288   -0.3332    0.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5222   -1.1899    0.9485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3059   -2.1635    0.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7219   -0.5480   -1.5939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2974   -2.0746   -0.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3541    0.3048    0.9056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8571   -1.3196    1.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2033    2.4865   -0.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4862    2.4499   -0.6934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9381    1.6249   -0.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4342    0.5794   -1.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3363   -0.0110   -0.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6168   -1.1716   -0.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3726   -3.0599    0.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0070    1.4840   -1.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2218    2.4585   -0.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  2  0
 19 20  1  0
  6 21  1  0
 21 22  2  0
 22  3  1  0
 19 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
 13 32  1  0
 14 33  1  0
 17 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 20 38  1  0
 21 39  1  0
 22 40  1  0
M  END

  Mrv1652308231919532D          

 22 23  0  0  0  0            999 V2000
    2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  1  0  0  0  0
 11  3  2  0  0  0  0
 11  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 13  9  2  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 16 10  2  0  0  0  0
 17 14  1  0  0  0  0
 17 15  2  0  0  0  0
 17 16  1  0  0  0  0
 18 14  2  0  0  0  0
 19 15  1  0  0  0  0
 20 16  1  0  0  0  0
 21  1  1  0  0  0  0
 21 12  1  0  0  0  0
 22  2  1  0  0  0  0
 22 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0055302

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(CCC(=O)C2=C(O)C=C(OC)C=C2O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H18O5/c1-21-12-6-3-11(4-7-12)5-8-14(18)17-15(19)9-13(22-2)10-16(17)20/h3-4,6-7,9-10,19-20H,5,8H2,1-2H3

> <INCHI_KEY>
VVDZZNWYISOIDK-UHFFFAOYSA-N

> <FORMULA>
C17H18O5

> <MOLECULAR_WEIGHT>
302.326

> <EXACT_MASS>
302.11542368

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
31.89382313618427

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(2,6-dihydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)propan-1-one

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
4.187328644666666

> <ALOGPS_LOGS>
-4.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.19680975866299

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.884429802263616

> <JCHEM_PKA_STRONGEST_BASIC>
-4.539825979928339

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
82.6719

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
calomelanone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-AUG-19         0                                  
HETATM    1  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335  10.780   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3    6   11                                                       
CONECT    4    7   11                                                       
CONECT    5    8   11                                                       
CONECT    6    3   12                                                       
CONECT    7    4   12                                                       
CONECT    8    5   14                                                       
CONECT    9   13   15                                                       
CONECT   10   13   16                                                       
CONECT   11    3    4    5                                                  
CONECT   12    6    7   21                                                  
CONECT   13    9   10   22                                                  
CONECT   14    8   17   18                                                  
CONECT   15    9   17   19                                                  
CONECT   16   10   17   20                                                  
CONECT   17   14   15   16                                                  
CONECT   18   14                                                            
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21    1   12                                                       
CONECT   22    2   13                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₈O₅

Average Mass

302.3260 Da

Monoisotopic Mass

302.11542 Da

IUPAC Name

1-(2,6-dihydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)propan-1-one

Traditional Name

calomelanone

CAS Registry Number

Not Available

SMILES

COC1=CC=C(CCC(=O)C2=C(O)C=C(OC)C=C2O)C=C1

InChI Identifier

InChI=1S/C17H18O5/c1-21-12-6-3-11(4-7-12)5-8-14(18)17-15(19)9-13(22-2)10-16(17)20/h3-4,6-7,9-10,19-20H,5,8H2,1-2H3

InChI Key

VVDZZNWYISOIDK-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Greyia flanaganii	LOTUS Database	35616633
Notholaena sulphurea	Plant	KNApSAcK
Pityrogramma calomelanos	Plant	KNApSAcK
Pityrogramma chrysophylla	Plant	KNApSAcK
Pityrogramma ebenea	LOTUS Database	35616633
Pityrogramma tartarea	Plant	KNApSAcK
Populus trichocarpa	Plant	KNApSAcK
Populus x jackii	Plant	KNApSAcK
Sarcandra glabra	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-hydroxy-dihydrochalcones. These are organic compounds containing dihydrochalcone skeleton that carries a hydroxyl group at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

2'-Hydroxy-dihydrochalcones

Alternative Parents

Substituents

2'-hydroxy-dihydrochalcone
Cinnamylphenol
Alkyl-phenylketone
Butyrophenone
Methoxyphenol
Phenylketone
Anisole
Benzoyl
Phenoxy compound
Phenol ether
Resorcinol
Aryl ketone
Aryl alkyl ketone
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Ether
Organic oxide
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120546 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.17	ALOGPS
logP	4.19	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	8.88	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	82.67 m³·mol⁻¹	ChemAxon
Polarizability	31.89 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0140286

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB093115

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3084606

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Calomelanone (NP0055302)

MOL for NP0055302 (Calomelanone)

3D MOL for NP0055302 (Calomelanone)

3D SDF for NP0055302 (Calomelanone)

3D-SDF for NP0055302 (Calomelanone)

PDB for NP0055302 (Calomelanone)

3D PDB for NP0055302 (Calomelanone)

SMILES for NP0055302 (Calomelanone)

INCHI for NP0055302 (Calomelanone)

Structure for NP0055302 (Calomelanone)

3D Structure for NP0055302 (Calomelanone)